The many Fantasies around my Small Penis

[SmallSub101]

This story will be centered around my many fantasies in different stages of life...(starting with middle school until married life... and everything in between). The fantasies center around my submissive attitude due to my small penis. Through the story, I have changed names to protect identities (including mine), and hope to be as thorough as possible.

Please leave criticism as you see fit, I probably will not change plot lines (after all these are MY fantasies) ,but if you wish to leave constructive criticism about how I tell the story, please go ahead

Let's begin.

Part 1: Middle School Pool Humiliation
Sam, known as Sammie to his peers, was 13 just introduced to the summer between 7th and 8th grade. He wasn't very popular among his classmates but he had a few close friends he played video games with and such. He was a skinny kid, much shorter than most of his grade as well.

You see, puberty had not been as kind to Sammie as it had been to others his age. His voice, still prepubescent and squeaky, and his lack of any body hair, made him a genuinely annoying specimen to others...
Not to mention his regular bullying by other larger classmates.

Regardless, Sammie was invited to a pool party at the public one right next to school with some of the popular children, around 30-40 people. A girl he fancied named Caitlyn (Cait) was a short brown haired beautiful girl with, let's say, a more defined body type than most girls her age.

-- Side note: Caitlyn had this on again, off again boyfriend that she broke up with right before the party. Name of Derrick, was ripped and had the most defined chest and abs of anyone their age. He was tall, dark, and handsome and could probably get any girl their age. What a guy. --

Caitlyn told him about this part out of pity, she knew Sammie liked her so much but he was just so immature and he had almost no friends, so why not play with him a little bit?

Sammie went to this pool party so excited to finally hang out with popular children his age and as soon as he got there he realized his great fear.

Caitlyn, and her friends Margaret and Amanda, were wearing skin tight bikinis and splashing around in the deep end of the pool.

The only issue... Sammie was deathly afraid of the water. Not to mention, his mom picked him up some tight speedo to wear that showed his, well let's go with "undeveloped", penis.

Sammie knew his one move he had to make at this party would be to start talking to Caitlyn and maybe make her laugh a little bit, so naturally, he went to go talk her up.

Let's outline her friends real quick to show who else Sammie had to encounter in his adventures of wooing Cait. There was Margaret, a rather large, muscly female who just happened to be a lesbian. She actually was one of the regular bullies of poor Sammie.

Amanda, a heartless bitch who showed no pity to Sammie and would not even look at him when he walked over to Caitlyn.

"Hi Cait, umm what's up?"

"Hi Sammie. Glad you came"

"Yeah um... same here"... his teenage awkwardness and lack of confidence showed around such a pretty girl.

"So... why don't you get in the water with us?"

"Oh. No thanks Caitlyn I'm really hungry and I guess I'll get in afterwards"

Margaret saw his weakness and once he went to turn she reached out of the pool and grabbed his speedo by the rear, exposing his little butt cheeks to most of the public pool.

"No, little guy. Caitlyn said get in the pool!"

With this, she grabbed him and threw him by the speedo into the public pool. What ensued was a lot of thrashing and splashing. Sammie searched desperately for the side of the pool and finally he grabbed on and pulled himself up gasping for air.

He quickly pulled up the speedo so his ass was no longer exposed and he slowly caught his breath... Amongst the crowd of laughter raining down on him.

The entire pool practically saw him get bullied by a GIRL. How would Caitlyn ever talk to him again.

He sat in shame, not before sneaking a glance at Cait and seeing her snicker. She had bigger plans in mind than this simple prank.

Sammie got used to the waters slightly but didn't really talk to anyone for a solid hour after that. He stayed in the pool but really never left the side wall.

He suddenly realized something, he looked down at his speedo and saw what he imagined was true, he had gotten one of his small erections that barely showed due to his small penis in regular pants, but this was a skin tight speedo and he was soaking wet. The entire outline of his penis was practically there for any passerby.

He turned his little boner to the wall of the pool and lifted his knees to block any side-view of it. He pretended like he was doing some sort of stretch.

Needless to say, this did not fool Amanda or Margaret.

Before doing this humping looking gesture to the wall, Amanda snuck a look at Sammie alone in the pool and saw his lackluster penis sticking out in the waters. He quickly moved to the wall and she whispered this to Margaret. She was going to humiliate him once again.

"Need some help there, Sammie? Looks like you have a little problem on your hands"

She quickly reached down and grabbed him by his hairless underarms. Strongly ripping him out of the water.

"Hey! STOP PLEASE"

Oh poor Sammie, he was only drawing more attention to his "little problem"

Everyone in the pool looked as she put him in a full-nelson that even a professional wrestler would be proud of. He was locked in.

"Wow Sammie, what's that sticking out between your legs? A baby carrot?"

Sammie was utterly humiliated as his erection was on full display for all to see, albeit covered by his thin speedo.

The laughter was booming. He closed his eyes but couldn't flush out the noise.

He struggled and struggled and she held him there for what felt like an eternity.

He opened his eyes during this humiliation, when she stopped thrashing him around to make his little penis swing side to side, and saw Caitlyn laughing her ass off with the rest of the pool.

He looked right next to Caitlyn, seeing Amanda and another face he knew too well. Derrick was right there laughing also.

After the little penis finally concluded it's erect state, he was finally released by this beast of a human known as Margaret, he ran to the bathroom crying and sniffling. He hid in the stall with a towel wrapped around him and contemplating when he should spring out of this hell hole and go home.

Just then he heard footsteps... like many sets of footsteps.

His fear increased... when he heard giggles.

He heard doors of the stalls opening and people searching. 1 by 1 they slowly approaches his in the corner of this men's bathroom. The cold floor touching his feet and was ready to make a run for it.

Speedo still on, shirtless with a towel wrapped around him. Sammie was sniffling and still had tears in his eyes, but Margaret still grabbed him and carried him to the open shower area. She was followed by none other than Caitlyn and Amanda.

"Please stop PLEASE ILL DO ANYTHING!!!" He yelled in between tears and sniffles.

"Shut up little bitch. Nothing will get you out of this. Caitlyn has known about your little crush for a long time. Time to finally show her what your working with"

"Caitlyn tell her to stop PLEASE ILL LEAVE YOU ALONE FOREVER"

"Oh no little guy... after what happened out there I wanted to see what you were really hiding under that tight ass speedo"... after saying this Caitlyn whipped out a ruler she stole from the front desk of the pool.

Sammie was going to get measured... and most likely his life would change from this moment on.

He was pinned to the ground and was unable to shift from Margaret's grip. Caitlyn was left to do the honors of pulling his speedo down and revealing his penis.

Sammie felt the cold floor on his back, this shower area smelled awful but that wasn't the most pressing issue in his life. His current love interest was about to see him at his most vulnerable.

He was crying, snot covered his area between his mouth and nose, his please of "please stop" "I'll do anything" "Caitlyn PLEASE OH MY GOD" meant nothing to these girls who clearly just wanted to get a laugh out of his little itty bitty penis.

Caitlyn made a show out of this experience.

She bent over in front of his face, exposing a gorgeous top view of her plump tits, and took her palm and gave a tight squeeze in his crotch area.

"Wow... let's hope it looks bigger than it seems, little guy"

This demeaning tone made sammies heart skip... it was the first contact his crotch had with a female, yet it wasn't in the way he wanted.

She slowly dragged his speedo down exposing his hairless genitals... and his balls and dick all in a cluster and shrunk due to the pool water.

Immediately laughter ensued

"OH MY GOD HOW SMALL IS IT?"
"WHAT THE FUCK? HAHAHA"
"CAITLYN HURRY MEASURE IT"
"ARE YOU SURE ITS A PENIS. OH MY GOD WHERES HIS HAIR DID HE WAX IT ALL OFF OR SOMETHING"

This one really hurt, "CAITLYN DIDNT YOU SAY DERRICK WAS LIKE 7 INCHES? DID LITTLE SAMMIE HERE REALLY THINK HE HAD A CHANCE?"

He was humiliated. And worst thing was... he started crying a lot this time. He balled his eyes out. Tears went down his face he sniffles and he looked like a crying fool. He could barely see, but he saw Caitlyn use the ruler on his soft little dicklette.

"1 1/4 INCHES!" "WOW BABY DICK, YOU BARELY HAVE ANYTHING THERE. ARE YOU SURE IT ISNT A LITTLE VAGINA?"

He sadly started to get aroused with one of the pretties girls in school mocking his most private secret, his erection stuck straight up with pride... at a whopping "OH MY GOD 2 3/4 INCHES!! WHAT THE FUCK IS THIS LITTLE PIN DICK SISSY BITCH?" "CAITLYN OH MY GOD I CANT BREATHE! ITS SO TINY HAHAHA"

Amanda pitched in "Cait... why don't you give him a little pleasure."

All three simultaneously went "oooooh" and caitlyn slowly bent over yet again and took her index finger and her thumb and started stroking him.

Not that this didn't feel good to him, it was just the circumstance he was put under.

His small 2 and then some inch cicumsized erect penis was being stroked by another girl... and she was laughing historically.

About a minute into this giggle session he felt the urge to cum... and it started to build, and just then he heard more footsteps.

Derrick just then ran into the bathroom screaming, "WHAT THE FUCK IS THIS"

"Oh shut up derrick get out of here... we're just having a little fun"

"CAIT WTF BABY. THIS LITTLE BITCH THINKS HE CAN GET A HANDY FROM YOU? ILL TEACH HIM!"

Sammie was grabbed, while naked, and thrown outside of the lockeroom. His little boner bouncing all over the place. He was promptly beaten to a pulp in front of all his classmates and every popular kid.

His erection went down, but the kids did not stop laughing as Derrick put bruises all over Sammie's body.

"NOW GET THE FUCK OUT OF HERE" derrick yelled at Sammie before kicking him in his dick and balls. Causing intense pain and he crouched over and grabbed his crotch.

Sammie quickly ran out of there with one hand covering his tiny, bruised dick and balls. He had to run the whole way home naked just like this, humiliated and crying more and more.

There were a few honks on the way home from passerby cars, but Sammie was already hurt and nothing could really damage him anymore.

He snuck in the house and ran to his room to ball his eyes out and curse his prepubescent penis.

--

This was the first of many torments to come in later parts for poor Sammie. The next story will be from the high school-post high school stage in his life.

Hopefully you enjoyed part one of the story, again any constructive criticism left will be taken into consideration and is encouraged! Tell me if you enjoyed it!

If you have any questions about my personal life (yes that is the actual size of my penis that I put in the story) please PM me, I love SPH!

Thanks for taking the time to read! New part coming soon!

[SmallSub101]

Part 2: The Bondage Chamber

-- Prelude: Sammie is now post-high-school. I was debating on whether or not to include some sort of hanging wedgie torture from Margaret/Caitlyn/Amanda in the previous chapter while he was still in high school. May still do it later on if someone requests it, but I wanted to do this bondage part next.

This is Sammie's first bondage experience and he is well on his way to becoming a full small dicked submissive, and not willingly. This is the chapter where the verbal humiliation gets to him and in the next part you will see how it affects his later life choices.

Thanks for reading everyone and enjoy the next part in the series --


It was the day after graduation and Sammie was in his parents' house on the couch watching ESPN. It had been a long high school career, and he was glad it was now over.

Sammie changed a lot since his middle school humiliation, he now grows pubic, chest, and hair under his arms. He shaves every strand of it, from his chin to his ass. Sammie never understood why he did this but he hated the look body hair on him, he liked looking like a prepubescent child for some reason.

During the commercials, Sammie began scrolling through twitter on his phone. He still had the same friends from around middle school and none of them really ever snap chatted him, so it was weird when he saw *Cait_2047 just added you!* alert him.

He saw the name "Cait" and his mind went back to all the humiliation he received at the pool that day...
... and how his penis has not grown a centimeter since then. His dick was still the size of an infant child.

Maybe saying that is even an insult to the infant because his 2.5 inch hard dick was pitiful. He remained a virgin through High School due to his lack of confidence, and the only real contact his dick ever had was the fateful day at the pool in middle school.

He was a true loser, and he was ashamed of himself.

He quickly clicked on that Snapchat notification and added Cait back, he hoped so much it was Caitlyn from high school. Why was she adding him now? They never talked after all through the rest of his school years.

A Snapchat from her popped up, it was a blue square representing a text message of sorts.

-- In this instance C will represent Caitlyn and S for Sammie --

C- "Hey Sammie!"
S- "Hey, are you Caitlyn from high school?"
C- "Yup! Happy Graduation!"
S- "Happy to finally be done!"
C- "Any big plans now that we are done?"
S- "I'm attending the local community college. How about you?"
C- "I'm undecided honestly, but I know college just isn't for me. So listen..."
S- "What's up?"
C- "I'm really sorry about what happened in middle school Sammie. Those girls are jerks and I told them I never want to see them once school was over. I just want us to be friends again"
S- "Caitlyn its fine, water under the bridge!"
C- "Are you sure? I was a completely different person then compared to now"
S- "Both of us have changed a lot since then, so I understand haha"
C- "I would hope so ... anyways how's about you come chill at my house tonight around 9 or so and we can get caught up"
S- "Sounds like a plan Cait, send your address and I'll bring a pizza or something"
C- "Ok!"

The plans were set and Sammie could not have more mixed emotions than now.

He had a chance with one of the prettiest girls in school, and in 4 years she had turned into the prettiest girl at the school by far. An amazingly fat ass and boobs. And she only really had been with a few guys and had one boyfriend during this time. Derrick and her were not on speaking terms anymore after their big fight.

On the other hand, if she did make a move on him he had no sexual experience. Not too mention the lack of any sort of penis to pleasure her. He hoped just to get to know her tonight and not have to whip out his lackluster dick.

The time had come and he was dressed in a relatively nice outfit. Good clothes for a relaxing evening watching movies and such.

He pulled up the house and rang the door bell, pizza in hand. She met him with open arms.

"SAMMIE! So good to see you!"

"Haha. Good to see you too"

After the hug, they came inside and started to dig into the pizza while catching up.

After the usual questions of "how have you been" had passed they got more personal and uneasy for Sammie.

"So since that day at the pool I'm guessing you're a little um... more endowed?" She said this while giggling and cracking a smile.

"Oh of course" he said with confidence "that was a while ago"

"Well good. Because I've been wanting to get with you for a while"

No more words were said. She grabbed him and took him downstairs to the basement. There was only one main room in this basement area. But there was a TV in the corner with a couch and she took him to it.

They lay here for about an hour, watching Breaking Bad and not really speaking. She was snuggled up against him, her ass right above his dick. They were practically spooning after not talking for years.

She finally made the first move and turned around and starting making out with him. This was actually his first kiss ever and he was not very good at it. They started getting more in depth as she took of her shirt and interrupted their make out session as she waited for him to do the same.

Her boobs looked fantastic in her bra and Sammie started to get a hardon. He removed his shirt and started getting nervous because no matter what eventually she would realize his penis is too small.

"You know... I never did get to finish you off at the pool that day... maybe I can finish the job today"

Sammie never got a chance to speak because she pounced on him. Placing her ass in his face and pinning him to the ground. She still had pants on but still this around Sammie like no other.

She looked at his crotch and saw the risining erection.

"Mmmm... let's get a look at that dick Sammie. Let's see if you really have grown since that day."

"MMMPHHHH" were the only words Sammie could get out as he was muffled by Caitlyn's amazing ass.

Sammie felt his waistband slowly lower, and his dick and boxers sprung out. Caitlyn quickly removed these and saw the most dissapointing sight ever.

His 2.5 inch hard penis on full display. Probably about an inch in girth and the average size of a human pinky (oh the irony, all the pinky wiggling he has seen and it's mostly accurate)

From under her ass cheeks he heard the laughter,

"OH MY GOD! Just like I remember it Sammie! Did you ever hit puberty all these years?"
"AND WHERE IS YOUR BODY HAIR? IM PRETTY SURE MY LITTLE 7 YEAR OLD COUSINS IS BIGGER THAN THAT!"

Sammie felt the tears coming. He could tell that she never wanted to sleep with him. She only wanted to humiliate him some more.

"You know, I had heard about that shrimp dick from the guys in the lockerroom and just had to see it for myself. Let's see how it cums."

"Sammie had his legs promptly tied up by Caitlyn. He could do nothing to prevent it. She picked Sammie up and took him to a pole and tied his hands around it so he had no movement.

Sammie was then ball gagged and blind folded. Caitlyn had the trap set and Margaret and Amanda made their way downstairs.

Margaret always had something to say, "Wow! You really haven't grown at all since middle school bitch dick!"

"That is still the smallest penis I have ever seen... and I've slept with like 50 guys dude... it's so sad" Amanda chimed in.

"He's here all for us, girls. I guess we should try and make that little thing cum first, we tried to before and never got to finish!"

"Caitlyn go ahead and get him going"

Caitlyn took her thumb and pointer finger and stroked his little boner up and down. She started going really fast and with a combination of the girls watching, the humiliation, and the bondage it took him one minute to bust his little load.

"Well that was quick!"

Caitlyn cleaned it off her hand with a tissue and took sammies ball gag off.

"DO NOT SAY A WORD OR WE WILL CUT IT OFF! UNDERSTAND?"

"Yes! Please don't hurt me!"

"Shut up bitch!" Caitlyn said as she shoved the cum covered tissue in Sammie's mouth and put the ball gag back in.

Sammie was clearly grossed out from the cum but he had no other option, he just had to deal with it.

"What now girls?"

"I want to see what that little thing feels like inside of me, someone wrap it up and I'll ride him!... if he cums while he's in me I guess we will just have Margaret take care of him."

Whatever this meant, made Sammie feel uneasy about it. But Amanda was about to ride him and he didn't know how he felt about it. The cum still in his mouth, he waited.

Amanda undressed and took off her thong, her glorious shaven vagina showing. Too bad Sammie was blindfolded.

She crouched down and prepared to attempt to ride this maggot dick.

"I can't find it... where is it?" She said between giggles.

She finally found it and sat down on the baby dicklette until there was nothing else to ride.

"WHAT THE FUCK? Is it in? HAHHAHA"

All the girls began laughing historically at Sammie as she bounced up and down and said she wouldn't know the difference between this and her pinky finger!

She eventually got off and said it was the most pathetic dick she ever rode. But Sammie did not cum.

"Wow... guess I have to finish him off, huh girls?"

Caitlyn got down on all fours to give him another handjob, she had other intentions for this one though.

She started pumping with her two fingers and Sammie started to pump his hips and soon shot his small load.

Caitlyn the asked Sammie "are you ready" and started forcefully yanking the little dick all over giving him a post orgasm torture that would make any man cringe.

First Sammie started squirming, then the muffled screams started coming out. After they removed the blindfold they realized he was actually crying badly. They almost felt bad because of the pain in his eyes.

She would not stop though, as she tormented Sammie for ever believeing he was a true guy saying "how dare you think you could actually please me with this!" "You should be ashamed of yourself QUIT CRYING BITCH BOY!"

She finally stopped after sammies entire face was covered in snot and tears and it was running down his cheeks. The entire two inch length of his penis was red and he could not stop crying.

The blindfold was reapplied and Sammie was about to become the sissy that was always inside of him.

Margaret's voice was heard, "how dare you try and fuck my best friend with your little pin dick. Actually, come to think of it, you're more of a girl than a guy at this point. You want to see what I do you my little girls that I fuck?"

Sammie knew exactly where this was going and tried to squirm out of his ties, but it was too late. His legs were untied and spread apart and the fake 6 inch dick was strapped on to Margaret.

"Tell me how this feels little bitch dick"

Sammie screamed when the dick first entered him, and after they took off his blindfold so they could see him cry, he started balling his eyes out. Every pump from Margaret led to another scream from Sammie. He was in pure pain.

She fucked him for about 25 minutes, before sticking a vibrating dildo in his ass and taping it shut.

"There, now he lost his anal virginity before his actual virginity. Because he doesn't deserved to fuck a girl, just to get dicked down like a girl"

Satisfied with their job they left Sammie here as he came all over himself and his dicklette throughout the night while the girls sat on the couch and watched the rest of breaking bad.

Sammies life would change forever after this, as he was now the sissy bitch he was always meant to be. That dick of his was never meant to fuck women.

--

Thanks for reading, part 3 coming soon!
Hope you enjoyed this second installment!
Let me know what you thought, thanks again!